Methyl 10-O-tert-Butyldimethylsilyl-oleanolate | 197500-50-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: Methyl 10-O-tert-Butyldimethylsilyl-oleanolate
• 英文别名: methyl (4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-[tert-butyl(dimethyl)silyl]oxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate
• CAS: 197500-50-8
• 化学式: C₃₇H₆₄O₃Si
• 分子量: 584.999
• InChiKey: PFXQUFDRMQZVJI-RRLKWQEHSA-N

物化性质

• 沸点：
  564.6±50.0 °C(Predicted)
• 密度：
  1.00±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  10.35
• 重原子数：
  41
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Methyl 10-O-tert-Butyldimethylsilyl-oleanolate 在 lithium aluminium tetrahydride 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 生成
  参考文献：
  名称：

  [EN] COMPOSITIONS COMPRISING TRITERPENOIDS AND USES THEREOF FOR TREATING OPTIC NEUROPATHY
  [FR] COMPOSITIONS COMPRENANT DES TRITERPÉNOÏDES ET LEURS UTILISATIONS POUR TRAITER UNE NEUROPATHIE OPTIQUE

  摘要：

  该发明涉及包含至少一种三萜酸和至少一种中性三萜类化合物的组合物和配方，以及用于治疗视神经病症的用途。

  公开号：

  WO2018047175A1
• 作为产物：
  描述：

  齐墩果酸 在 咪唑 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 Methyl 10-O-tert-Butyldimethylsilyl-oleanolate
  参考文献：
  名称：

  [EN] COMPOSITIONS COMPRISING TRITERPENOIDS AND USES THEREOF FOR TREATING OPTIC NEUROPATHY
  [FR] COMPOSITIONS COMPRENANT DES TRITERPÉNOÏDES ET LEURS UTILISATIONS POUR TRAITER UNE NEUROPATHIE OPTIQUE

  摘要：

  该发明涉及包含至少一种三萜酸和至少一种中性三萜类化合物的组合物和配方，以及用于治疗视神经病症的用途。

  公开号：

  WO2018047175A1

文献信息

• Chemical Phenotypes of the hmg1 and hmg2 Mutants of Arabidopsis Demonstrate the In-planta Role of HMG-CoA Reductase in Triterpene Biosynthesis
  作者：Kiyoshi Ohyama、Masashi Suzuki、Kazuo Masuda、Shigeo Yoshida、Toshiya Muranaka

  DOI：10.1248/cpb.55.1518

  日期：——

  Plants produce a wide variety of cyclic triterpenes, such as sterols and triterpenoids, which are the major products of the mevalonate (MVA) pathway. It is important to understand the physiological functions of HMG-CoA reductase (HMGR) because HMGR is the rate-limiting enzyme in the MVA pathway. We have previously isolated Arabidopsis mutants in HMG1 and HMG2. Although the biochemical function of HMGR2 has been thought to be almost equal to that of HMGR1, based on similarities in their sequences, the phenotypes of mutants in these genes are quite different. Whereas hmg2 shows no abnormal phenotype under normal growth conditions, hmg1 shows pleiotropic phenotypes, including dwarfing, early senescence, and male sterility. We previously postulated that the 50% decrease in the sterol content of hmg1, as compared to that in the wild type, was a cause of these phenotypes,1) but comprehensive triterpene profiles of these mutants had not yet been determined. Here, we present the triterpene profiles of hmg1 and hmg2. In contrast to hmg1, hmg2 showed a sterol content 15% lower than that of the wild type. A precise triterpenoid quantification using synthesized deuterated compounds of β-amyrin (1), α-amyrin (2), and lupeol (3) showed that the levels of triterpenoids in hmg1 and hmg2 were 65% and 25% lower than in the wild type (WT), respectively. These results demonstrate that HMGR2 as well as HMGR1 is responsible for the biosynthesis of triterpenes in spite of the lack of visible phenotypes in hmg2.

  植物产生多种环状三萜，如固醇和三萜类化合物，这些是梅瓦龙酸（MVA）途径的主要产物。了解HMG-CoA还原酶（HMGR）的生理功能非常重要，因为HMGR是MVA途径中的限速酶。我们之前已经分离出阿拉伯芥中HMG1和HMG2的突变体。虽然基于它们序列的相似性，HMGR2的生化功能被认为几乎与HMGR1相同，但这些基因突变体的表型却大相径庭。HMG2在正常生长条件下没有显示出异常表型，而HMG1则表现出多重表型，包括矮小、早衰和雄性不育。我们之前推测，HMG1的固醇含量比野生型降低50%是这些表型的原因之一，但这些突变体的全面三萜谱尚未确定。在这里，我们呈现HMG1和HMG2的三萜谱。与HMG1相比，HMG2的固醇含量比野生型低15%。使用合成的重氢化合物β-氨瑞烯（1）、α-氨瑞烯（2）和露蓉醇（3）进行的精确三萜类化合物定量显示，HMG1和HMG2中的三萜类化合物水平分别比野生型低65%和25%。这些结果表明，虽然HMG2缺乏明显的表型，但HMGR2和HMGR1均负责三萜的生物合成。
• [EN] COMPOSITIONS COMPRISING TRITERPENOIDS<br/>[FR] COMPOSITIONS COMPRENANT DES TRITERPÉNOÏDES
  申请人：REGENERA PHARMA LTD

  公开号：WO2017051423A1

  公开（公告）日：2017-03-30

  The invention relates to compositions and formulations comprising at least one triterpenoic acid and at least one neutral triterpenoid and uses thereof for treating for use in treating a condition selected from Alzheimer's disease (AD), Parkinson's Diseases (PD) and vascular dementia (VD).

  该发明涉及包含至少一种三萜酸和至少一种中性三萜类化合物的组合物和配方，以及它们用于治疗阿尔茨海默病（AD）、帕金森病（PD）和血管性痴呆（VD）等疾病的用途。
• Partial Synthesis of Krukovines A and B, Triterpene Ketones Isolated from the Brazilian Medicinal Plant <i>Maytenus</i> <i>krukovii</i>
  作者：Tadashi Honda、Heather J. Finlay、Gordon W. Gribble

  DOI：10.1021/np9702897

  日期：1997.11.1

  Krukovines A (1) and B (2): triterpene ketones isolated from the Brazilian medicinal plant ''chuchuhuasi'' (Maytenus krukovii), were synthesized in eight steps from the commercially available oleanolic acid and ursolic acid, respectively.